Marine General to Defense Intel Agency (DIA)

Could a teenage immigrant from a Caribbean island become a Marine General and advisor to U.S. Presidents? This determined individual proved it was possible. 

FAMILY BACKGROUND

Vincent Raymond Stewart (“VS”) was born in Kingston, Jamaica. He was raised mainly by his mother, a domestic worker who spent two years in Bermuda, working and saving money, so that she could afford to move her son, then age 13, and his older sister to the United States. 

CHILDHOOD 

VS recalled the pain he felt, after immigrating as a teenager, where as a young Black man in Chicago, “I felt I had no future beyond manual, low-skilled labor, and any dreams of being a leader or owning a business were out of the question.” He was stopped by police “nearly every time” he left his home and was intimidated by a local sheriff.

It wouldn’t be the last time VS had to cope with racial prejudice / discrimination, but he vowed to himself to try to stay positive and set a better example for others. 

EDUCATION

After arriving in the ‘States,’ the family settled on the North side of Chicago, where VS attended public schools, played football, and won an athletic scholarship to college, where he majored in history courses. Coincidentally, that school’s nickname was the ‘Fighting Leathernecks’ – a name long and widely used to informally refer to members of the U.S. Marine Corps. (“Corps” is pronounced “Cor”). 

MARINE SERVICE

Following college graduation, VS decided upon a career in military service, aiming to be an officer as soon as possible, for the dual goals of being a leader and at the same time, avoiding being the victim of racism. 

VS completed Marine officer training, a combination of boot camp to weed out the physically and mentally unfit plus education in basic military functions including leadership skills, military weapons proficiency, introduction to survival tactics and respecting the ‘chain of command.’ He was recognized as one of the top scoring officer candidates upon being proudly commissioned as a 2^nd Lieutenant, USMC. 

Gen. Stewart recalled that when he joined the Marines, he hoped to be “part of something bigger” after working as a door-to-door encyclopedia salesman during college. He planned to serve in the military for just a few years, but instead remained in the Marines for nearly four decades, rising from a position as a tank-unit platoon leader to become the nation’s highest-ranking military intelligence officer while simultaneously serving as a Marine Corps Lieutenant General. 

CHALLENGE – COPING WITH RACISM

VS believed that as a young Marine officer, he was sometimes passed over for prominent military assignments while being described as “the unit’s best Black officer,” rather than its “best officer.” 

His response was simply to avoid outwardly reacting to perceived prejudice and instead, devote himself to being a better Marine and a better leader of men. 

VS found success in part through the mentorship of trailblazing Black military officers, such as Army General Colin L. Powell. He was also helped along by White officers such as (now retired) Marine General / Marine Corps Commandant and Chairman of the Joint Chiefs of Staff, Joseph Dunford, who gained an appreciation for General Stewart during the Iraq War, when Gen. Stewart served for a time as the head of military intelligence efforts in the western Anbar province. 

“People wanted to be on his team,” Dunford recalled. “He was one of those people where when he asked how you were doing, if you were a subordinate, he was waiting for an answer.” In essence, VS cared about his troops, and they appreciated it. 

Dunford, asked about the barriers that Gen. Stewart faced, said that his friend and colleague “knew it might be harder for him than others” and believed that “he could overcome obstacles by outworking others.”

DEFENSE INTELLIGENCE AGENCY (D.I.A.) SERVICE

As head of the Defense Intelligence Agency from January 2015 to October 2017, VS advised the President (first Obama, then Trump), lawmakers and the Chairman of the Joint Chiefs of Staff on global threats and national security issues, including the strength of Taliban fighters in Afghanistan, the impact of Russian troops on the Syrian civil war, and the progress of North Korea’s nuclear weapon and advanced missile programs. 

“Let’s focus on understanding the adversary’s military capabilities so that we can prevent war, VS told a national security website in 2016, outlining his priorities. “And if we can’t prevent war, let’s beat the stuffings out of anyone who comes against us.”

When Gen. Stewart took over the DIA, becoming the first Marine Corps officer to serve as Director, a U.S.-led coalition was fighting to beat back an Islamic State insurgency that had swept across Syria and Iran. He predicted accurately that the militant group wanted to establish branches in Afghanistan, Yemen, and several African nations. He was later credited with playing a key role in developing U.S. Cyber Command, where he concluded his career as Deputy Commander before retiring and starting his own consulting firm. 

While leading the DIA, Gen. Stewart shifted its focus from counterterrorism to what he characterized as “long-term existential threats” including from China, Russia, North Korea, and Iran. He also worked to deepen partnerships with U.S. allies, notably by creating a new position – Deputy Director for Commonwealth Integration – held on a rotating basis by officials from America’s intelligence partners in the “Five Eyes” alliance, which includes Australia, Britain, Canada and New Zealand.

Within the DIA, Gen. Stewart sought to strengthen workplace culture by creating a DIA Museum and establishing fitness and worship centers at the agency’s headquarters. 

“He gave this persona of a battle-hardened Marine,” said a fellow Marine Lt. General, “but when you got inside him, there was a bit of a softer approach there.” 

AN ACTIVE RETIREMENT

While many senior military officers settle quietly into retirement, Gen. Stewart made occasional headlines, including when he criticized then President Trump for inciting rioters during the Jan. 6, 2021, attack on the U.S. Capitol. 

He said that after years in which he had “encouraged other countries to follow our lead” in abiding by democratic principles, “it will be extremely difficult delivering that message now. When China cracks down on dissidents, how can we offer ‘rule of law’ as the best approach?” 

Gen. Stewart also spoke out against racial injustice, both in and out of the military. The death of George Floyd, who died under the boot of a Minneapolis police officer, “has personally impacted me and saddened me for our country,” wrote Gen. Stewart in an Op-ed. He said that he “will always believe in the promise of America, because if the dream is not possible here, it’s not possible anywhere.”

“As a person who has had incredible success in this country, I am directly appealing to those in positions of power and privilege to recognize the experiences of your fellow Americans who do not look like you. Learn from them and take meaningful actions to lift them up. And I want you to imagine what our country would look like then.”

CAREER SATISFACTION

Gen. Stewart’s successor as Director of the DIA said that he “was a larger-than-life presence at DIA, known for initiating sweeping changes and modernization efforts that continue to benefit the nation’s intelligence gathering.”

“Everywhere he’s gone,” said James Clapper, VS’ predecessor at the DIA, “he’s perfected the basics of intelligence work.”

A Commandant of the Marine Corps, Gen. David H. Berger, described Gen. Stewart as “a trailblazer, a selfless leader, and a mentor,” adding that “his impact as a leader of Marines and the broader intelligence community cannot be understated.”

During his career, Gen. Stewart received military honors including the Defense Distinguished Service Medal, Navy Distinguished Service Medal, Defense Superior Service Medal, two decorations of the Legion of Merit and the Bronze Star. But he always downplayed his achievements, such as when he was once asked about his ‘secret to success’ and responded, “I showed up, most of the time, on time and occasionally in the right uniform. And I didn’t implode.”

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This career story is based on an obituary written by Harrison Smith and Dan Lamothe, published by The Washington Post on May 1, 2023, plus internet research.